α-oxygenated or α-thiolated carboxylic acid phenethylamide derivatives
Abstract
The invention relates to α-oxygenated or α-thiolated carboxylic acid phenethylamide derivatives of the general formula I including the optical isomers thereof and mixtures of such isomers, wherein A stands for optionally substituted aryl or optionally substituted heteroaryl; X is oxygen or sulfur; Y is oxygen or sulfur; R 1 is hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl, haloalkyl, haloalkenyl, haloalkynyl or halocycloalkyl; R 2 is hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, alkoxy-alkyl, alkoxy-alkenyl, alkoxy-alkynyl, whereof all alkyl-alkenyl-, alkynyl-, or cycloalkyl-groups me be optionally substituted by halogen; or optionally substituted arylalkyl, optionally substituted-aryl-alkenyl, optionally substituted aryl-alkynyl or optionally substituted aryloxy-alkyl; R 3 is hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkyl-alkyl, alkoxy-alkyl, alkoxy-alkenyl, alkoxy-alkynyl, whereof all alkyl-alkenyl-, alkynyl-, or cycloalkyl-groups me be optionally substituted by halogen; or is optionally substituted aryl-alkyl, optionally substituted aryl-alkenyl, optionally substituted aryl-alkynyl, optionally substituted aryloxy-alkyl, optionally substituted heteroaryl-alkyl, optionally substituted heteroaryl-alkenyl or optionally substituted heteroaryl-alkynyl; R 4 is alkyl, alkenyl, alkynyl, alkoxy-alkyl, alkoxy, alkenyloxy, alkynyloxy, alkylthio, alkanoyl, alkylamino, dialkylamino, alkoxycarbonyl, whereof all alkyl-alkenyl or alkynyl-groups may be optionally substituted by halogen; or is halogen, cyano, nitro, amino, formyl or carboxyl; R 5 is hydrogen, alkyl, alkenyl or alkynyl; n is an integer 0, 1, 2, 3, or 4; B 1 represents a bridge member —(CR 10 R 11 ) q — or —(CHR 10 R 11 ) r -Z-(CR 12 R 13 ) 8 , wherein q is an integer 2, 3 or 4; r is an integer 0, 1; 2, 3; s is an integer 1, 2 or 3, provided that (r+s) is either 1, 2 or 3; Z is —O—, —S—, —SO— —SO2-, NR 6 —, —CO—, —OOC—, —COO—, —NR 6 —CO— or —CO—NR 6 —; R 6 is hydrogen or alkyl; R 10 , R 11 , R 12 and R 13 independently of each other are hydrogen or alkyl; and B 2 is an alkylene bridge. These compounds possess useful plant protecting properties and may advantageously be employed in agricultural practice for controlling or preventing the infestation of plants by phytopathogenic microorganisms, especially fungi.
Claims
exact text as granted — not AI-modified1. A compound of the formula
the optical isomers and mixtures of such isomers thereof, wherein A is phenyl, naphthyl, 1,3-biphenyl, 1,4-biphenyl, fluorenyl, tetralinyl, indanyl, methylendioxyphenyl or (1,2-ethylene)dioxyphenyl, each optionally substituted by one or more substituents selected from the group consisting of C 1 -C 10 -alkyl, C 2 -C 10 -alkenyl, C 2 -C 10 -alkynyl, C 1 -C 8 -cycloalkyl, C 1 -C 8 -cycloalkyl-C 1 -C 10 -alkyl, phenyl, phenyl-C 1 -C 10 -alkyl, C 1 -C 10 -alkoxy, C 3 -C 10 -alkenyloxy, C 3 -C 10 -alkynyloxy, C 1 -C 10 -alkylthio, C 1 -C 10 -alkylsulfonyl, C 1 -C 10 -alkoxy-C 1 -C 10 -alkyl, C 1 -C 10 -alkanoyl, C 1 -C 10 -alkoxycarbonyl, C 3 -C 10 -alkenyloxycarbonyl, C 3 -C 10 -alkynyloxycarbonyl, C 1 -C 10 -alkylamino, di-C 1 -C 10 -alkylamino, hydroxy, halogen, cyano, nitro, amino and formyl radicals, wherein in turn the alkyl- alkenyl-, alkynyl- and cycloalkyl-groups may be optionally substituted by one or more halogen atoms;
X is oxygen or sulfur;
Y is oxygen or sulfur;
R 1 is hydrogen, C 1 -C 10 -alkyl, C 3 -C 10 -alkenyl, C 3 -C 10 -alkynyl or C 3 -C 8 -cycloalkyl, wherein all alkyl- alkenyl-, alkynyl- and cycloalkyl-groups may be optionally substituted by halogen; and
R 2 is hydrogen, C 1 -C 10 -alkyl, C 3 -C 10 -alkenyl, C 3 -C 10 -alkynyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -cycloalkyl-C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy-C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy-C 3 -C 10 -alkenyl or C 1 -C 6 -alkoxy-C 3 -C 10 -alkynyl, wherein all alkyl- alkenyl-, alkynyl-, or cycloalkyl-groups may be optionally substituted by halogen; or stands for phenyl-C 1 -C 6 -alkyl, phenyl-C 1 -C 6 -alkenyl or phenyl-C 1 -C 6 -alkynyl, wherein phenyl may optionally be mono- or disubstituted by substituents selected from the group consisting of C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkylthio, C 1 -C 6 -haloalkylthio, C 1 -C 6 -alkanoyl, C 1 -C 6 -alkoxycarbonyl, halogen, cyano, nitro and formyl; and
R 3 is hydrogen, C 1 -C 10 -alkyl, C 3 -C 10 -alkenyl, C 3 -C 10 -alkynyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -cycloalkyl-C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy-C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy-C 3 -C 10 -alkenyl or C 1 -C 6 -alkoxy-C 3 -C 10 -alkynyl, wherein all alkyl- alkenyl-, alkynyl-, or cycloalkyl-groups may be optionally substituted by halogen; or is phenyl-C 1 -C 6 -alkyl, phenyl-C 1 -C 6 -alkenyl or phenyl-C 1 -C 6 -alkynyl, wherein the phenyl groups are optionally mono- or disubstituted by radicals selected from the group consisting of C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkylthio, C 1 -C 6 -haloalkylthio, C 1 -C 6 -alkanoyl, C 1 -C 6 -alkoxycarbonyl, halogen, cyano, nitro and formyl; and
R 4 is C 1 -C 6 -alkyl, C 3 -C 6 -alkenyl, C 3 -C 6 -alkynyl, C 1 -C 6 -alkoxy-C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy, C 3 -C 6 -alkenyloxy, C 3 -C 6 -alkynyloxy, C 1 -C 6 -alkylthio, C 1 -C 6 -alkanoyl, C 1 -C 6 -alkylamino, di-C 1 -C 6 -alkylamino or C 1 -C 6 -alkoxycarbonyl, wherein all alkyl- alkenyl or alkynyl-groups may be optionally substituted by halogen; or is halogen, cyano, nitro, amino, formyl or carboxyl; and
R 5 is hydrogen, C 1 -C 6 -alkyl, C 3 -C 6 -alkenyl or C 3 -C 6 -alkynyl;
n is an integer 0, 1, 2, 3, or 4;
B 1 represents a bridge member —(CR 10 R 11 ) q — or —(CHR 10 R 11 ) r -Z-(CR 12 R 13 ) s , wherein
q is an integer 2, 3 or 4;
r is an integer 0, 1, 2, 3; s is an integer 1, 2 or 3, provided that (r+s) is either 1, 2 or 3;
Z is —O—, —S—, —SO—, —SO 2 —, NR 6 —, —CO—, —OOC—, —COO—, —NR 6 —CO— or —CO—NR 6 —;
R 6 is hydrogen or C 1 -C 4 alkyl;
R 10 , R 11 , R 12 and R 13 independently of each other are hydrogen or C 1 -C 4 alkyl; and
B 2 is an C 1 -C 6 -alkylene bridge.
2. A compound according to claim 1 , wherein n is an integer from 0 to 2.
3. A compound according to claim 1 , wherein A is phenyl, naphthyl, 1,4-biphenyl, tetralinyl, indanyl, methylendioxyphenyl or (1,2-ethylene)dioxyphenyl, each optionally substituted by one, two or three substituents selected from the group consisting of C 1 -C 10 -alkyl, C 1 -C 10 -haloalkyl, C 2 -C 10 -alkenyl, C 2 -C 10 -haloalkenyl, C 2 -C 10 -alkynyl, benzyl, C 1 -C 10 -alkoxy, C 1 -C 10 -haloalkoxy, C 3 -C 10 -alkenyloxy, C 3 -C 10 -alkynyloxy, C 1 -C 10 -alkylthio, C 1 -C 10 -haloalkylthio, C 1 -C 10 -alkylsulfonyl, C 1 -C 6 -alkoxy-C 1 -C 6 -alkyl, C 1 -C 10 -alkanoyl, C 1 -C 10 -alkoxycarbonyl, hydroxy, halogen, cyano, nitro and formyl.
4. A compound of formula I according to claim 1 , wherein A is phenyl, naphthyl, 1,4-biphenyl, tetralinyl, indanyl, methylendioxyphenyl or (1,2-ethylene)dioxyphenyl, each optionally substituted by one, two or three substituents selected from the group consisting of C 1 -C 10 -alkyl, C 1 -C 10 -haloalkyl, C 2 -C 10 -alkenyl, C 2 -C 10 -haloalkenyl, C 2 -C 10 -alkynyl, benzyl, C 1 -C 10 -alkoxy, C 1 -C 10 -haloalkoxy, C 3 -C 10 -alkenyloxy, C 3 -C 10 -alkynyloxy, C 1 -C 10 -alkylthio, C 1 -C 10 -haloalkylthio, C 1 -C 10 -alkylsulfonyl, C 1 -C 6 -alkoxy-C 1 -C 6 -alkyl, C 1 -C 10 -alkanoyl, C 1 -C 10 -alkoxycarbonyl, hydroxy, halogen, cyano, nitro and formyl; and X is oxygen or sulfur; and Y is oxygen or sulfur; and R 1 is hydrogen, C 1 -C 10 -alkyl, C 3 -C 10 -alkenyl, C 3 -C 10 -alkynyl, C 1 -C 10 -haloalkyl, C 3 -C 10 -haloalkenyl or C 3 -C 10 -haloalkynyl; and R 2 is hydrogen, C 1 -C 10 -alkyl, C 3 -C 10 -alkenyl, C 3 -C 10 -alkynyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -cycloalkyl-C 1 -C 6 -alkyl, C 3 -C 8 -cycloalkyl-C 3 -C 6 -alkenyl, C 3 -C 8 -cycloalkyl-C 3 -C 6 -alkynyl, C 1 -C 6 -alkoxy-C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy-C 3 -C 6 -alkenyl, C 1 -C 6 -alkoxy-C 3 -C 6 -alkynyl, C 1 -C 10 -haloalkyl, C 3 -C 10 -haloalkenyl, C 3 -C 10 -haloalkynyl, phenyl-C 1 -C 6 -alkyl, phenyl-C 1 -C 6 -alkenyl or phenyl-C 1 -C 6 -alkynyl, wherein phenyl may optionally be mono- or disubstituted by substituents selected from the group consisting of C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkylthio, C 1 -C 6 -haloalkylthio, C 1 -C 6 -alkanoyl, C 1 -C 6 -alkoxycarbonyl, halogen, cyano, nitro and formyl; and R 3 is hydrogen, C 1 -C 10 -alkyl, C 3 -C 10 -alkenyl, C 3 -C 10 -alkynyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -cycloalkyl-C 1 -C 6 -alkyl, C 3 -C 8 -cycloalkyl-C 3 -C 6 -alkenyl, C 3 -C 8 -cycloalkyl-C 3 -C 6 -alkynyl, C 1 -C 6 -alkoxy-C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy-C 3 -C 6 -alkenyl, C 1 -C 6 -alkoxy-C 3 -C 3 -C 6 -alkynyl, C 1 -C 10 -haloalkyl, C 3 -C 10 -haloalkenyl, C 3 -C 10 -haloalkynyl, phenyl-C 1 -C 6 -alkyl, phenyl-C 1 -C 6 -alkenyl or phenyl-C 1 -C 6 -alkynyl, wherein the phenyl groups are optionally mono- or disubstituted by radicals selected from the group consisting of C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkylthio, C 1 -C 6 -haloalkylthio, C 1 -C 6 -alkanoyl, C 1 -C 6 -alkoxycarbonyl, halogen, cyano, nitro and formyl; and R 4 is C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 3 -C 6 -alkenyloxy, C 3 -C 6 -alkynyloxy, C 1 -C 6 -alkylthio, halogen, cyano or nitro; and R 5 is hydrogen, C 1 -C 6 -alkyl, C 3 -C 6 -alkenyl or C 3 -C 6 -alkynyl; and n is an integer from 0 to 2; and B 2 is an alkylene-bridge of the formula —CH(R 20 )—(CH 2 ) p —, wherein R 20 stands for hydrogen or C 1 -C 4 -alkyl and p is an integer 0, 1 or 2.
5. A compound of formula I according to claim 1 , wherein A is phenyl, naphthyl, 1,4-biphenyl, tetralinyl, indanyl or methylendioxyphenyl, each optionally substituted by one, two or three substituents selected from the group consisting of C 1 -C 10 -alkyl, C 1 -C 10 -haloalkyl, C 2 -C 10 -alkenyl, C 2 -C 10 -alkynyl, benzyl, C 1 -C 10 -alkoxy, C 1 -C 10 -haloalkoxy, C 1 -C 10 -alkylthio, C 1 -C 10 -haloalkylthio, C 1 -C 10 -alkanoyl, C 1 -C 10 -alkoxycarbonyl, halogen, cyano, nitro and formyl; and X is oxygen or sulfur; and Y is oxygen or sulfur; and R 1 is hydrogen, C 1 -C 8 -alkyl, C 3 -C 8 -alkenyl or C 3 -C 8 -alkynyl; and R 2 stands for hydrogen, C 1 -C 8 -alkyl, C 3 -C 8 -alkenyl, C 3 -C 8 -alkynyl, C 3 -C 6 -cycloalkyl-C 3 -C 4 -alkynyl, C 1 -C 4 -alkoxy-C 3 -C 4 -alkynyl, C 1 -C 8 -haloalkyl or C 3 -C 8 -haloalkynyl; and R 3 is hydrogen, C 1 -C 8 -alkyl, C 3 -C 8 -alkenyl, C 3 -C 8 -alkynyl, C 3 -C 6 -cycloalkyl-C 3 -C 4 -alkynyl, C 1 -C 4 -alkoxy-C 3 -C 4 -alkynyl, C 1 -C 8 -haloalkyl or C 3 -C 8 -haloalkynyl; and R 4 is C 1 -C 6 -alkoxy, C 3 -C 6 -alkenyloxy, C 3 -C 6 -alkynyloxy or halogen; and R 5 is hydrogen or C 1 -C 4 -alkyl; and B 1 stands for a bridge member —(CR 10 R 11 ) q — or —(CHR 10 R 11 ) r -Z-(CR 12 R 13 ) s , wherein R 10 , R 11 , R 12 and R 13 independently of each other are hydrogen or C 1 -C 4 -alkyl, q is the integer 2, r is the integer 0; s is the integer 1, and Z is —O—, —S— or —CO—; and n is the integer 0 or 1; and B 2 is an alkylene-bridge of the formula —CH(R 20 )—(CH 2 ) p —, wherein R 20 stands for hydrogen or C 1 -C 4 -alkyl and p is an integer 0, 1 or 2.
6. A compound of formula I according to claim 1 , wherein A is phenyl, optionally substituted by one or two substituents selected from the group consisting of C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 2 -C 4 -alkenyl, C 1 -C 4 -alkoxy, C 1 -C 10 -alkylthio, C 1 -C 4 -alkanoyl, halogen and cyano; and X is oxygen; and Y is oxygen; and R 1 is hydrogen, C 1 -C 8 -alkyl, C 3 -C 8 -alkenyl or C 3 -C 8 -alkynyl; and R 2 is hydrogen, C 1 -C 8 -alkyl, C 3 -C 8 -alkenyl, C 3 -C 8 -alkynyl, C 3 -C 6 -cycloalkyl-C 3 -C 4 -alkynyl or C 1 -C 4 -alkoxy-C 3 -C 4 -alkynyl; and R 3 is hydrogen, C 1 -C 8 -alkyl, C 3 -C 8 -alkenyl, C 3 -C 8 -alkynyl, C 3 -C 6 -cycloalkyl-C 3 -C 4 -alkynyl or C 1 -C 4 -alkoxy-C 3 -C 4 -alkynyl; and R 4 is 3-C 1 -C 6 -alkoxy; and R 5 is hydrogen or methyl; and B 1 is selected from —CH 2 —CH 2 —, —O—CH 2 — and —S—CH 2 —; and n is the integer 0 or 1; and B 2 is —CH 2 —CH 2 —, CH 2 —, CH(CH 3 )—CH 2 — or CH(CH 3 )—.
7. A compound according to claim 1 , wherein A is phenyl, optionally substituted by one or two substituents selected from the group consisting of C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, halogen and cyano; and X and Y are both oxygen; and R 1 is hydrogen; and R 2 is hydrogen, C 1 -C 4 -alkyl, C 3 -C 4 -alkenyl or C 3 -C 4 -alkynyl; and R 3 is C 1 -C 4 -alkyl, C 3 -C 4 -alkenyl or C 3 -C 4 -alkynyl; and R 4 is 3-methoxy or 3-ethoxy; and R 5 is hydrogen; and B 1 is selected from —CH 2 —CH 2 —, —O—CH 2 — and —S—CH 2 —; and n is the integer 1; and B 2 is —CH 2 —CH 2 —.
8. A compound of formula I according to claim 1 , selected from the group consisting of
2-hydroxy-N-[2-(3-methoxy-4-prop-2-ynyloxy-phenyl)-ethyl]-4-phenyl-butyramide,
2-methoxy-N-[2-(3-methoxy-4-prop-2-ynyloxy-phenyl)-ethyl]-4-phenyl-butyramide,
2-ethoxy-N-[2-(3-methoxy-4-prop-2-ynyloxy-phenyl)-ethyl]-4-phenyl-butyramide,
N-[2-(3-methoxy-4-prop-2-ynyloxy-phenyl)-ethyl]-4-phenyl-2-prop-2-ynyloxy-butyramide,
2-hydroxy-N-[2-(3-methoxy-4-prop-2-ynyloxy-phenyl)-ethyl]-4-p-tolyl-butyramide,
2-methoxy-N-[2-(3-methoxy-4-prop-2-ynyloxy-phenyl)-ethyl]-4-p-tolyl-butyramide,
2-ethoxy-N-[2-(3-methoxy-4-prop-2-ynyloxy-phenyl)-ethyl]-4-p-tolyl-butyramide,
N-[2-(3-methoxy-4-prop-2-ynyloxy-phenyl)-ethyl]-2-prop-2-ynyloxy-4-p-tolyl-butyramide,
4-(4-fluoro-phenyl)-2-hydroxy-N-[2-(3-methoxy-4-prop-2-ynyloxy-phenyl)-ethyl]-butyramide,
4-(4-fluoro-phenyl)-2-methoxy-N-[2-(3-methoxy-4-prop-2-ynyloxy-phenyl)-ethyl]-butyramide,
2-ethoxy-4-(4-fluoro-phenyl)-N-[2-(3-methoxy-4-prop-2-ynyloxy-phenyl)-ethyl]-butyramide,
4-(4-fluoro-phenyl)-N-[2-(3-methoxy-4-prop-2-ynyloxy-phenyl)-ethyl]-2-prop-2-ynyloxy-butyramide,
4-(4-chloro-phenyl)-2-hydroxy-N-[2-(3-methoxy-4-prop-2-ynyloxy-phenyl)-ethyl]-butyramide,
4-(4-chloro-phenyl)-2-methoxy-N-[2-(3-methoxy-4-prop-2-ynyloxy-phenyl)-ethyl]-butyramide,
4-(4-chloro-phenyl)-2-ethoxy-N-[2-(3-methoxy-4-prop-2-ynyloxy-phenyl)-ethyl]-butyramide,
4-(4-chloro-phenyl)-N-[2-(3-methoxy-4-prop-2-ynyloxy-phenyl)-ethyl]-2-prop-2-ynyloxy-butyramide,
2-hydroxy-N-[2-(3-methoxy-4-prop-2-ynyloxy-phenyl)-ethyl]-3-phenoxy-propionamide,
2-methoxy-N-[2-(3-methoxy-4-prop-2-ynyloxy-phenyl)-ethyl]-3-phenoxy-propionamide,
2-ethoxy-N-[2-(3-methoxy-4-prop-2-ynyloxy-phenyl)-ethyl]-3-phenoxy-propionamide,
N-[2-(3-methoxy-4-prop-2-ynyloxy-phenyl)-ethyl]-3-phenoxy-2-prop-2-ynyloxy-propionamide,
2-hydroxy-N-[2-(3-methoxy-4-prop-2-ynyloxy-phenyl)-ethyl]-3-p-tolyloxy-propionamide,
2-methoxy-N-[2-(3-methoxy-4-prop-2-ynyloxy-phenyl)-ethyl]-3-p-tolyloxy-propionamide,
2-ethoxy-N-[2-(3-methoxy-4-prop-2-ynyloxy-phenyl)-ethyl]-3-p-tolyloxy-propionamide,
N-[2-(3-methoxy-4-prop-2-ynyloxy-phenyl)-ethyl]-2-prop-2-ynyloxy-3-p-tolyloxy-propionamide,
3-(4-ethyl-phenoxy)-2-hydroxy-N-[2-(3-methoxy-4-prop-2-ynyloxy-phenyl)-ethyl]-propionamide,
3-(4-ethyl-phenoxy)-2-methoxy-N-[2-(3-methoxy-4-prop-2-ynyloxy-phenyl)-ethyl]-propionamide,
2-ethoxy-3-(4-ethyl-phenoxy)-N-[2-(3-methoxy-4-prop-2-ynyloxy-phenyl)-ethyl]-propionamide,
3-(4-ethyl-phenoxy)-N-[2-(3-methoxy-4-prop-2-ynyloxy-phenyl)-ethyl]-2-prop-2-ynyloxy-propionamide,
3-(4-fluoro-phenoxy)-2-hydroxy-N-[2-(3-methoxy-4-prop-2-ynyloxy-phenyl)-ethyl]-propionamide,
3-(4-fluoro-phenoxy)-2-methoxy-N-[2-(3-methoxy-4-prop-2-ynyloxy-phenyl)-ethyl]-propionamide,
2-ethoxy-3-(4-fluoro-phenoxy)-N-[2-(3-methoxy-4-prop-2-ynyloxy-phenyl)-ethyl]-propionamide,
3-(4-fluoro-phenoxy)-N-[2-(3-methoxy-4-prop-2-ynyloxy-phenyl)-ethyl]-2-prop-2-ynyloxy-propionamide,
3-(4-chloro-phenoxy)-2-hydroxy-N-[2-(3-methoxy-4-prop-2-ynyloxy-phenyl)-ethyl]-propionamide,
3-(4-chloro-phenoxy)-2-methoxy-N-[2-(3-methoxy-4-prop-2-ynyloxy-phenyl)-ethyl]-propionamide,
3-(4-chloro-phenoxy)-2-ethoxy-N-[2-(3-methoxy-4-prop-2-ynyloxy-phenyl)-ethyl]-propionamide,
3-(4-chloro-phenoxy)-N-[2-(3-methoxy-4-prop-2-ynyloxy-phenyl)-ethyl]-2-prop-2-ynyloxy-propionamide,
3-(3,4-dichloro-phenoxy)-2-hydroxy-N-[2-(3-methoxy-4-prop-2-ynyloxy-phenyl)-ethyl]-propionamide,
3-(3,4-dichloro-phenoxy)-2-methoxy-N-[2-(3-methoxy-4-prop-2-ynyloxy-phenyl)-ethyl]-propionamide,
3-(3,4-dichloro-phenoxy)-2-ethoxy-N-[2-(3-methoxy-4-prop-2-ynyloxy-phenyl)-ethyl]-propionamide, -3-(3,4-dichloro-phenoxy)-N-[2-(3-methoxy-4-prop-2-ynyloxy-phenyl)-ethyl]-2-prop-2-ynyloxy-propionamide,
2-hydroxy-N-[2-(3-methoxy-4-prop-2-ynyloxy-phenyl)-ethyl]-3-phenylthio-propionamide,
2-methoxy-N-[2-(3-methoxy-4-prop-2-ynyloxy-phenyl)-ethyl]-3-phenylthio-propionamide,
2-ethoxy-N-[2-(3-methoxy-4-prop-2-ynyloxy-phenyl)-ethyl]-3-phenylthio-propionamide,
N-[2-(3-methoxy-4-prop-2-ynyloxy-phenyl)-ethyl]-3-phenylthio-2-prop-2-ynyloxy-propionamide,
3-(4-chloro-phenylthio)-2-hydroxy-N-[2-(3-methoxy-4-prop-2-ynyloxy-phenyl)-ethyl]-propionamide, 3-(4-chloro-phenylthio)-2-methoxy-N-[2-(3-methoxy-4-prop-2-ynyloxy-phenyl)-ethyl]-propionamide,
3-(4-chloro-phenylthio)-2-ethoxy-N-[2-(3-methoxy-4-prop-2-ynyloxy-phenyl)-ethyl]-propionamide,
3-(4-chloro-phenylthio)-N-[2-(3-methoxy-4-prop-2-ynyloxy-phenyl)-ethyl]-2-prop-2-ynyloxy-propionamide,
3-benzyloxy-2-hydroxy-N-[2-(3-methoxy-4-prop-2-ynyloxy-phenyl)-ethyl]-propionamide,
3-benzyloxy-2-methoxy-N-[2-(3-methoxy-4-prop-2-ynyloxy-phenyl)-ethyl]-propionamide,
3-benzyloxy-2-ethoxy-N-[2-(3-methoxy-4-prop-2-ynyloxy-phenyl)-ethyl]-propionamide,
3-benzyloxy-N-[2-(3-methoxy-4-prop-2-ynyloxy-phenyl)-ethyl]-2-prop-2-ynyloxy-propionamide,
3-(4-chloro-benzyloxy)-2-hydroxy-N-[2-(3-methoxy-4-prop-2-ynyloxy-phenyl)-ethyl]-propionamide,
3-(4-chloro-benzyloxy)-2-methoxy-N-[2-(3-methoxy-4-prop-2-ynyloxy-phenyl)-ethyl]-propionamide,
3-(4-chloro-benzyloxy)-2-ethoxy-N-[2-(3-methoxy-4-prop-2-ynyloxy-phenyl)-ethyl]-propionamide, 3-(4-chloro-benzyloxy)-N-[2-(3-methoxy-4-prop-2-ynyloxy-phenyl)-ethyl]-2-prop-2-ynyloxy-propionamide,
(R)-2-hydroxy-N-[2-(3-methoxy-4-prop-2-ynyloxy-phenyl)-ethyl]-4-phenyl-butyramide,
(R)-2-methoxy-N-[2-(3-methoxy-4-prop-2-ynyloxy-phenyl)-ethyl]-4-phenyl-butyramide,
(R)-2-ethoxy-N-[2-(3-methoxy-4-prop-2-ynyloxy-phenyl)-ethyl]-4-phenyl-butyramide,
(R)-N-[2-(3-methoxy-4-prop-2-ynyloxy-phenyl)-ethyl]-4-phenyl-2-prop-2-ynyloxy-butyramide,
(R)-2-hydroxy-N-[2-(3-methoxy-4-prop-2-ynyloxy-phenyl)-ethyl]-4-p-tolyl-butyramide,
(R)-2-methoxy-N-[2-(3-methoxy-4-prop-2-ynyloxy-phenyl)-ethyl]-4-p-tolyl-butyramide,
(R)-2-ethoxy-N-[2-(3-methoxy-4-prop-2-ynyloxy-phenyl)-ethyl]-4-p-tolyl-butyramide,
(R)-N-[2-(3-methoxy-4-prop-2-ynyloxy-phenyl)-ethyl]-2-prop-2-ynyloxy-4-p-tolyl-butyramide,
(R)-4-(4-fluoro-phenyl)-2-hydroxy-N-[2-(3-methoxy-4-prop-2-ynyloxy-phenyl)-ethyl]-butyramide,
(R)-4-(4-fluoro-phenyl)-2-methoxy-N-[2-(3-methoxy-4-prop-2-ynyloxy-phenyl)-ethyl]-butyramide,
(R)-2-ethoxy-4-(4-fluoro-phenyl)-N-[2-(3-methoxy-4-prop-2-ynyloxy-phenyl)-ethyl]-butyramide,
(R)-4-(4-fluoro-phenyl)-N-[2-(3-methoxy-4-prop-2-ynyloxy-phenyl)-ethyl]-2-prop-2-ynyloxy-butyramide,
(R)-4-(4-chloro-phenyl)-2-hydroxy-N-[2-(3-methoxy-4-prop-2-ynyloxy-phenyl)-ethyl]-butyramide,
(R)-4-(4-chloro-phenyl)-2-methoxy-N-[2-(3-methoxy-4-prop-2-ynyloxy-phenyl)-ethyl]-butyramide,
(R)-4-(4-chloro-phenyl)-2-ethoxy-N-[2-(3-methoxy-4-prop-2-ynyloxy-phenyl)-ethyl]-butyramide,
(R)-4-(4-chloro-phenyl)-N-[2-(3-methoxy-4-prop-2-ynyloxy-phenyl)-ethyl]-2-prop-2-ynyloxy-butyramide,
(R)-2-hydroxy-N-[2-(3-methoxy-4-prop-2-ynyloxy-phenyl)-ethyl]-3-phenoxy-propionamide,
(R)-2-methoxy-N-[2-(3-methoxy-4-prop-2-ynyloxy-phenyl)-ethyl]-3-phenoxy-propionamide,
(R)-2-ethoxy-N-[2-(3-methoxy-4-prop-2-ynyloxy-phenyl)-ethyl]-3-phenoxy-propionamide,
(R)-N-[2-(3-methoxy-4-prop-2-ynyloxy-phenyl)-ethyl]-3-phenoxy-2-prop-2-ynyloxy-propionamide,
(R)-2-hydroxy-N-[2-(3-methoxy-4-prop-2-ynyloxy-phenyl)-ethyl]-3-p-tolyloxy-propionamide,
(R)-2-methoxy-N-[2-(3-methoxy-4-prop-2-ynyloxy-phenyl)-ethyl]-3-p-tolyloxy-propionamide,
(R)-2-ethoxy-N-[2-(3-methoxy-4-prop-2-ynyloxy-phenyl)-ethyl]-3-p-tolyloxy-propionamide,
(R)-N-[2-(3-methoxy-4-prop-2-ynyloxy-phenyl)-ethyl]-2-prop-2-ynyloxy-3-p-tolyloxy-propionamide,
(R)-3-(4-ethyl-phenoxy)-2-hydroxy-N-[2-(3-methoxy-4-prop-2-ynyloxy-phenyl)-ethyl]-propionamide,
(R)-3-(4-ethyl-phenoxy)-2-methoxy-N-[2-(3-methoxy-4-prop-2-ynyloxy-phenyl)-ethyl]-propionamide,
(R)-2-ethoxy-3-(4-ethyl-phenoxy)-N-[2-(3-methoxy-4-prop-2-ynyloxy-phenyl)-ethyl]-propionamide,
(R)-3-(4-ethyl-phenoxy)-N-[2-(3-methoxy-4-prop-2-ynyloxy-phenyl)-ethyl]-2-prop-2-ynyloxy-propionamide,
(R)-3-(4-fluoro-phenoxy)-2-hydroxy-N-[2-(3-methoxy-4-prop-2-ynyloxy-phenyl)-ethyl]-propionamide,
(R)-3-(4-fluoro-phenoxy)-2-methoxy-N-[2-(3-methoxy-4-prop-2-ynyloxy-phenyl)-ethyl]-propionamide,
(R)-2-ethoxy-3-(4-fluoro-phenoxy)-N-[2-(3-methoxy-4-prop-2-ynyloxy-phenyl)-ethyl]-propionamide,
(R)-3-(4-fluoro-phenoxy)-N-[2-(3-methoxy-4-prop-2-ynyloxy-phenyl)-ethyl]-2-prop-2-ynyloxy-propionamide,
(R)-3-(4-chloro-phenoxy)-2-hydroxy-N-[2-(3-methoxy-4-prop-2-ynyloxy-phenyl)-ethyl]-propionamide,
(R)-3-(4-chloro-phenoxy)-2-methoxy-N-[2-(3-methoxy-4-prop-2-ynyloxy-phenyl)-ethyl]-propionamide,
(R)-3-(4-chloro-phenoxy)-2-ethoxy-N-[2-(3-methoxy-4-prop-2-ynyloxy-phenyl)-ethyl]-propionamide,
(R)-3-(4-chloro-phenoxy)-N-[2-(3-methoxy-4-prop-2-ynyloxy-phenyl)-ethyl]-2-prop-2-ynyloxy-propionamide,
(R)-3-(3,4-dichloro-phenoxy)-2-hydroxy-N-[2-(3-methoxy-4-prop-2-ynyloxy-phenyl)-ethyl]-propionamide,
(R)-3-(3,4-dichloro-phenoxy)-2-methoxy-N-[2-(3-methoxy-4-prop-2-ynyloxy-phenyl)-ethyl]-propionamide,
(R)-3-(3,4-dichloro-phenoxy)-2-ethoxy-N-[2-(3-methoxy-4-prop-2-ynyloxy-phenyl)-ethyl]-propionamide,
(R)-3-(3,4-dichloro-phenoxy)-N-[2-(3-methoxy-4-prop-2-ynyloxy-phenyl)-ethyl]-2-prop-2-ynyloxy-propionamide,
(R)-2-hydroxy-N-[2-(3-methoxy-4-prop-2-ynyloxy-phenyl)-ethyl]-3-phenylthio-propionamide,
(R)-2-methoxy-N-[2-(3-methoxy-4-prop-2-ynyloxy-phenyl)-ethyl]-3-phenylthio-propionamide,
(R)-2-ethoxy-N-[2-(3-methoxy-4-prop-2-ynyloxy-phenyl)-ethyl]-3-phenylthio-propionamide,
(R)-N-[2-(3-methoxy-4-prop-2-ynyloxy-phenyl)-ethyl]-3-phenylthio-2-prop-2-ynyloxy-propionamide,
(R)-3-(4-chloro-phenylthio)-2-hydroxy-N-[2-(3-methoxy-4-prop-2-ynyloxy-phenyl)-ethyl]-propionamide,
(R)-3-(4-chloro-phenylthio)-2-methoxy-N-[2-(3-methoxy-4-prop-2-ynyloxy-phenyl)-ethyl]-propionamide,
(R)-3-(4-chloro-phenylthio)-2-ethoxy-N-[2-(3-methoxy-4-prop-2-ynyloxy-phenyl)-ethyl]-propionamide,
(R)-3-(4-chloro-phenylthio)-N-[2-(3-methoxy-4-prop-2-ynyloxy-phenyl)-ethyl]-2-prop-2-ynyloxy-propionamide,
(R)-3-benzyloxy-2-hydroxy-N-[2-(3-methoxy-4-prop-2-ynyloxy-phenyl)-ethyl]-propionamide,
(R)-3-benzyloxy-2-methoxy-N-[2-(3-methoxy-4-prop-2-ynyloxy-phenyl)-ethyl]-propionamide,
(R)-3-benzyloxy-2-ethoxy-N-[2-(3-methoxy-4-prop-2-ynyloxy-phenyl)-ethyl]-propionamide,
(R)-3-benzyloxy-N-[2-(3-methoxy-4-prop-2-ynyloxy-phenyl)-ethyl]-2-prop-2-ynyloxy-propionamide,
(R)-3-(4-chloro-benzyloxy)-2-hydroxy-N-[2-(3-methoxy-4-prop-2-ynyloxy-phenyl)-ethyl]-propionamide,
(R)-3-(4-chloro-benzyloxy)-2-methoxy-N-[2-(3-methoxy-4-prop-2-ynyloxy-phenyl)-ethyl]-propionamide,
(R)-3-(4-chloro-benzyloxy)-2-ethoxy-N-[2-(3-methoxy-4-prop-2-ynyloxy-phenyl)-ethyl]-propionamide,(R)-3-(4-chloro-benzyloxy)-N-[2-(3-methoxy-4-prop-2-ynyloxy-phenyl)-ethyl]-2-prop-2-ynyloxy-propionamide,
(S)-2-hydroxy-N-[2-(3-methoxy-4-prop-2-ynyloxy-phenyl)-ethyl]-4-phenyl-butyramide,
(S)-2-methoxy-N-[2-(3-methoxy-4-prop-2-ynyloxy-phenyl)-ethyl]-4-phenyl-butyramide,
(S)-2-ethoxy-N-[2-(3-methoxy-4-prop-2-ynyloxy-phenyl)-ethyl]-4-phenyl-butyramide,
(S)-N-[2-(3-methoxy-4-prop-2-ynyloxy-phenyl)-ethyl]-4-phenyl-2-prop-2-ynyloxy-butyramide,
(S)-2-hydroxy-N-[2-(3-methoxy-4-prop-2-ynyloxy-phenyl)-ethyl]-4-p-tolyl-butyramide,
(S)-2-methoxy-N-[2-(3-methoxy-4-prop-2-ynyloxy-phenyl)-ethyl]-4-p-tolyl-butyramide,
(S)-2-ethoxy-N-[2-(3-methoxy-4-prop-2-ynyloxy-phenyl)-ethyl]-4-p-tolyl-butyramide,
(S)-N-[2-(3-methoxy-4-prop-2-ynyloxy-phenyl)-ethyl]-2-prop-2-ynyloxy-4-p-tolyl-butyramide,
(S)-4-(4-fluoro-phenyl)-2-hydroxy-N-[2-(3-methoxy-4-prop-2-ynyloxy-phenyl)-ethyl]-butyramide,
(S)-4-(4-fluoro-phenyl)-2-methoxy-N-[2-(3-methoxy-4-prop-2-ynyloxy-phenyl)-ethyl]-butyramide,
(S)-2-ethoxy-4-(4-fluoro-phenyl)-N-[2-(3-methoxy-4-prop-2-ynyloxy-phenyl)-ethyl]-butyramide,
(S)-4-(4-fluoro-phenyl)-N-[2-(3-methoxy-4-prop-2-ynyloxy-phenyl)-ethyl]-2-prop-2-ynyloxy-butyramide,
(S)-4-(4-chloro-phenyl)-2-hydroxy-N-[2-(3-methoxy-4-prop-2-ynyloxy-phenyl)-ethyl]-butyramide,
(S)-4-(4-chloro-phenyl)-2-methoxy-N-[2-(3-methoxy-4-prop-2-ynyloxy-phenyl)-ethyl]-butyramide,
(S)-4-(4-chloro-phenyl)-2-ethoxy-N-[2-(3-methoxy-4-prop-2-ynyloxy-phenyl)-ethyl]-butyramide,
(S)-4-(4-chloro-phenyl)-N-[2-(3-methoxy-4-prop-2-ynyloxy-phenyl)-ethyl]-2-prop-2-ynyloxy-butyramide,
(S)-2-hydroxy-N-[2-(3-methoxy-4-prop-2-ynyloxy-phenyl)-ethyl]-3-phenoxy-propionamide,
(S)-2-methoxy-N-[2-(3-methoxy-4-prop-2-ynyloxy-phenyl)-ethyl]-3-phenoxy-propionamide,
(S)-2-ethoxy-N-[2-(3-methoxy-4-prop-2-ynyloxy-phenyl)-ethyl]-3-phenoxy-propionamide,
(S)-N-[2-(3-methoxy-4-prop-2-ynyloxy-phenyl)-ethyl]-3-phenoxy-2-prop-2-ynyloxy-propionamide,
(S)-2-hydroxy-N-[2-(3-methoxy-4-prop-2-ynyloxy-phenyl)-ethyl]-3-p-tolyloxy-propionamide,
(S)-2-methoxy-N-[2-(3-methoxy-4-prop-2-ynyloxy-phenyl)-ethyl]-3-p-tolyloxy-propionamide,
(S)-2-ethoxy-N-[2-(3-methoxy-4-prop-2-ynyloxy-phenyl)-ethyl]-3-p-tolyloxy-propionamide,
(S)-N-[2-(3-methoxy-4-prop-2-ynyloxy-phenyl)-ethyl]-2-prop-2-ynyloxy-3-p-tolyloxy-propionamide,
(S)-3-(4-ethyl-phenoxy)-2-hydroxy-N-[2-(3-methoxy-4-prop-2-ynyloxy-phenyl)-ethyl]-propionamide,
(S)-3-(4-ethyl-phenoxy)-2-methoxy-N-[2-(3-methoxy-4-prop-2-ynyloxy-phenyl)-ethyl]-propionamide,
(S)-2-ethoxy-3-(4-ethyl-phenoxy)-N-[2-(3-methoxy-4-prop-2-ynyloxy-phenyl)-ethyl]-propionamide,
(S)-3-(4-ethyl-phenoxy)-N-[2-(3-methoxy-4-prop-2-ynyloxy-phenyl)-ethyl]-2-prop-2-ynyloxy-propionamide,
(S)-3-(4-fluoro-phenoxy)-2-hydroxy-N-[2-(3-methoxy-4-prop-2-ynyloxy-phenyl)-ethyl]-propionamide,
(S)-3-(4-fluoro-phenoxy)-2-methoxy-N-[2-(3-methoxy-4-prop-2-ynyloxy-phenyl)-ethyl]-propionamide,
(S)-2-ethoxy-3-(4-fluoro-phenoxy)-N-[2-(3-methoxy-4-prop-2-ynyloxy-phenyl)-ethyl]-propionamide,
(S)-3-(4-fluoro-phenoxy)-N-[2-(3-methoxy-4-prop-2-ynyloxy-phenyl)-ethyl]-2-prop-2-ynyloxy-propionamide,
(S)-3-(4-chloro-phenoxy)-2-hydroxy-N-[2-(3-methoxy-4-prop-2-ynyloxy-phenyl)-ethyl]-propionamide,
(S)-3-(4-chloro-phenoxy)-2-methoxy-N-[2-(3-methoxy-4-prop-2-ynyloxy-phenyl)-ethyl]-propionamide,
(S)-3-(4-chloro-phenoxy)-2-ethoxy-N-[2-(3-methoxy-4-prop-2-ynyloxy-phenyl)-ethyl]-propionamide,
(S)-3-(4-chloro-phenoxy)-N-[2-(3-methoxy-4-prop-2-ynyloxy-phenyl)-ethyl]-2-prop-2-ynyloxy-propionamide,
(S)-3-(3,4-dichloro-phenoxy)-2-hydroxy-N-[2-(3-methoxy-4-prop-2-ynyloxy-phenyl)-ethyl]-propionamide,
(S)-3-(3,4-dichloro-phenoxy)-2-methoxy-N-[2-(3-methoxy-4-prop-2-ynyloxy-phenyl)-ethyl]-propionamide,
(S)-3-(3,4-dichloro-phenoxy)-2-ethoxy-N-[2-(3-methoxy-4-prop-2-ynyloxy-phenyl)-ethyl]-propionamide,
(S)-3-(3,4-dichloro-phenoxy)-N-[2-(3-methoxy-4-prop-2-ynyloxy-phenyl)-ethyl]-2-prop-2-ynyloxy-propionamide,
(S)-2-hydroxy-N-[2-(3-methoxy-4-prop-2-ynyloxy-phenyl)-ethyl]-3-phenylthio-propionamide,
(S)-2-methoxy-N-[2-(3-methoxy-4-prop-2-ynyloxy-phenyl)-ethyl]-3-phenylthio-propionamide,
(S)-2-ethoxy-N-[2-(3-methoxy-4-prop-2-ynyloxy-phenyl)-ethyl]-3-phenylthio-propionamide,
(S)-N-[2-(3-methoxy-4-prop-2-ynyloxy-phenyl)-ethyl]-3-phenylthio-2-prop-2-ynyloxy-propionamide,
(S)-3-(4-chloro-phenylthio)-2-hydroxy-N-[2-(3-methoxy-4-prop-2-ynyloxy-phenyl)-ethyl]-propionamide,
(S)-3-(4-chloro-phenylthio)-2-methoxy-N-[2-(3-methoxy-4-prop-2-ynyloxy-phenyl)-ethyl]-propionamide,
(S)-3-(4-chloro-phenylthio)-2-ethoxy-N-[2-(3-methoxy-4-prop-2-ynyloxy-phenyl)-ethyl]-propionamide,
(S)-3-(4-chloro-phenylthio)-N-[2-(3-methoxy-4-prop-2-ynyloxy-phenyl)-ethyl]-2-prop-2-ynyloxy-propionamide,
(S)-3-benzyloxy-2-hydroxy-N-[2-(3-methoxy-4-prop-2-ynyloxy-phenyl)-ethyl]-propionamide,
(S)-3-benzyloxy-2-methoxy-N-[2-(3-methoxy-4-prop-2-ynyloxy-phenyl)-ethyl]-propionamide,
(S)-3-benzyloxy-2-ethoxy-N-[2-(3-methoxy-4-prop-2-ynyloxy-phenyl)-ethyl]-propionamide,
(S)-3-benzyloxy-N-[2-(3-methoxy-4-prop-2-ynyloxy-phenyl)-ethyl]-2-prop-2-ynyloxy-propionamide,
(S)-3-(4-chloro-benzyloxy)-2-hydroxy-N-[2-(3-methoxy-4-prop-2-ynyloxy-phenyl)-ethyl]-propionamide,
(S)-3-(4-chloro-benzyloxy)-2-methoxy-N-[2-(3-methoxy-4-prop-2-ynyloxy-phenyl)-ethyl]-propionamide,
(S)-3-(4-chloro-benzyloxy)-2-ethoxy-N-[2-(3-methoxy-4-prop-2-ynyloxy-phenyl)-ethyl]-propionamide, and
(S)-3-(4-chloro-benzyloxy)-N-[2-(3-methoxy-4-prop-2-ynyloxy-phenyl)-ethyl]-2-prop-2-ynyloxy-propionamide.
9. A process for the preparation of a compound of formula I according to claim 1 , which comprises reacting
a) reacting the phenol of formula VI
wherein A, R 1 , R 2 , R 4 , R 5 , B 1 , B 2 and n are as defined for formula I with a compound of formula V
Z-R 3 (V)
wherein R 3 is as defined for formula I and wherein Z is a leaving group yielding the subgroup IA
b)reacting the acid of formula II
with an amine of formula VII
wherein A, R 1 , R 2 , R 3 , R 4 , R 5 , B 1 , B 2 and n are as defined for formula I, or
c) reacting the compound of formula XIV
with an etherifying agent of formula XV
Z-R 2 (XV)
wherein A, R 1 , R 2 , R 3 , R 4 , R 5 , B 1 , B 2 and n are as defined for formula I and wherein Z is a leaving group; yielding the subgroup IB
and optionally converting the amide function of the compound of subgroup IA into a thioamide function as in the subgroup IC
by treatment with a sulfurating agent.
10. A composition comprising a compound of formula I according to claim 1 as active ingredient together with a suitable carrier.
11. A method of controlling an infestation of crop plants by phytopathogenic fungi, which comprises the application of a compound of formula I according to claim 1 as active ingredient to the plant, to parts of plants or to the locus thereof.Cited by (0)
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